title: Easy access to fully functionalized chiral tetrahydro-β-carboline alkaloids.
abstract: A four-step synthetic route to fully substituted chiral tetrahydro-β-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan. tarai@faculty.chiba-u.jp
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Arai
authors.forename: Makiko
authors.initials: M
authors.lastname: Wasai
authors.forename: Naota
authors.initials: N
authors.lastname: Yokoyama
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry; D000627:Aminophenols / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D048288:Imidazolines / Q000737:chemistry; D015394:Molecular Structure; D009498:Neurotoxins / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D000627:Aminophenols; D002243:Carbolines; D048288:Imidazolines; D009498:Neurotoxins; C009804:tryptoline; D003300:Copper